If you are to run a quick Google search of “Winston Churchill” and view the image results, you are going to find two dominant results: A black and white photo of him sitting with his serious expression and a smiling Churchill with a fat cigar sticking out his mouth. As one of the most important political figures of the 20th century, Churchill did not only become famous for his oratorical skills and political leadership in the United Kingdom, especially during the war, but also for his trademark image of being a devoted smoker. A dangerous habit justified by the challenges that he had to face throughout his life and career.

A Habit That Started From a Young Age

Churchill was born to an A-list family on 30 November 1874: His dad was a politician and Parliament member, while his American mom was the daughter of a rich stockbroker, financier, and newspaper proprietor in New York. He would grow to admire the political successes of his dad, although their relationship would not be an easy one. On the other hand, his mom would not be able to provide her young son with the attention he yearned for.

Winston Churchill at Harrow School, 1892. (International Churchill Society)

As a student, he had to attend multiple boarding schools before barely passing his entrance exams for Harrow, one of Britain’s most elite schools. Soon, his parents would discover that not only was he not interested in studying, but he would also begin to smoke cigarettes with his classmates. His mother’s solution was to bribe him: She promised her son that she would give him a pony and a pistol if he stopped smoking and instead focused on school.

Discovering His Cuban Treasure

In 1895, just after graduating from the Royal Military Academy Sandhurst, Churchill was eager to put his name out there and gain experience, so he and a fellow officer visited Cuba as an observer of the ongoing conflict between the Cuban rebels and the Spanish colonialists. While there, and just like many other English officers of that time, he wanted to explore the attractions and delicacies that Cuba could offer, and that was how he found out about the love of his life: Cuban cigars.